EPISODE
837

The $30M app that lets you invest like a politician

Jun 30, 2026·70:00·Sam & Shaan·with Alex Daniels, Josh, Brian·Listen·AppleSpotify
0:0035:0070:00
22 moments · 696 paragraphs · synced to the second

All right. I own $40 million, $10 million in revenue.

JOSH

We acquire shit, and this year we'll generate around $20 million of revenue.

BRIAN

We manage shit, and that makes $30 million per year of revenue for the company.

SHAAN

Those are 3 ideas that didn't even exist in my, my cone of vision. You know, I didn't even know that people do businesses like that. I feel like I can rule the world. I know I could be what I want to. I put my all in it like no days off. On the road, let's try.

SAM

All right. How's it feel to be in real life? This is strange.

SHAAN

This is weird. It's been, uh, there's normally a screen right here. Actually, we should put a side by side of the last time we were in person in San Francisco doing it on the red chairs.

SAM

So when we, um, when you started this thing and then I came on 2 or 3 months later, we had these bright red chairs that we bought off Amazon for $150 and it was just us sitting on chairs and I hated it because you could like see like a crotch shot.

SHAAN

Yeah, I think I might be doing it now.

SAM

And you're just like sitting like this. And then we had a, like a camcorder.

SHAAN

We would have a guy in the room and we'd be like, hey, are we good to go? Is it all good? Audio, video? And he'd be like, I think so. It was like, I think so is like not what you want to hear from the guy who's just setting up the camera.

SAM

He was my summer intern.

SHAAN

Yeah.

SAM

And it was one camera.

SHAAN

You ever done audio video before? No.

SAM

But I hear you.

SHAAN

Yeah. Yeah. I can hear you great.

SAM

What do you think of New York? You been to a bodega yet?

SHAAN

Yeah, we went to a bodega.

SAM

Yeah. So I talk about bodega culture. I don't know if you've like seen any that have impressed you. Have you seen any that have impressed you?

SHAAN

I have to like stay out of bodegas because I just start chatting it up for too long.

SAM

It's the best, right?

SHAAN

Like, dude, I've been here for 75 minutes talking to this guy.

SAM

Like the, like the cashier. Yeah, it's the best. I'm friends with so many bodega owners.

SHAAN

We could do a full MFM just inside a bodega. I probably should have done that actually.

SAM

And like, it's the pure definition of entrepreneurship because you could clearly tell like, oh, one day someone asked for cereal. Now they have 10 Costco-sized things of cereal and they're individually packed into an ice coffee cup and they just sell cereal now. Like, that's just what they do. There's no like, does this go with our mission statement? Like, no, we sell cereal now, right? I don't know if you need a license to sell food, even though it says don't repackage this for individual sale. We sell cereal now, right? And that's what I love. All right. So today we're doing something a little bit special. You said you were coming and I reached out. I basically just Slacked like the Hampton channel. I go, who in New York has like an odd business that we can like impress Sean with? And so we picked 3 different entrepreneurs.

They have—

SAM

I tried to find 3 businesses that were off the beaten path a little bit because that's why people like watching MFM. You guys like watching or seeing like kind of strange businesses. So hopefully you can open up your mind and be like, oh, there's a million ways to get done whatever I want to get done and build a big company, right? So I picked 3.

SHAAN

Okay.

SAM

Okay. So they're going to come on. What are they going to do?

SHAAN

So we told them, we just bumped into them. We just told them, hey, come in here and don't start with words.

This is MFM.

SHAAN

You got to start with a number. And, um, don't make us dig it out of you. Just give it to us. You know the shtick. You know what we like to do. We like to know everything. We like you to not be humble and brag about that. We want you to brag a little. So they're going to say a number, they're going to say what they do, and then we're going to get to know their business because we're nerdy about businesses. And then at the end, you know, we will ask them two things. We'll ask them what adjacent business opportunities are there. Like what other businesses do they see because of where they are in their tiny niche that we don't have enough exposure to that other people might go run at. And then two, like, how can we help them? Like, what's the, what's the burning question? What if they just had me and you for like, you know, 10 minutes? What would they want to talk to us about? So that's what we're going to try.

BRIAN

All right.

SHAAN

The first guy, Ben, we could bring him in. What's up?

How you doing?

SHAAN

All right. Welcome to the podcast.

BRIAN

Thanks.

SAM

All right. So I've known Alex for years. For a year.

Yeah. A year.

SAM

A year. We're very good friends, so I'm going to be biased. Okay, start us off with the big number.

All right. I have 4— I own 40 publications, 40 magazines, $10 million in revenue.

SHAAN

40 magazines, $10 million in revenue.

Yeah.

SHAAN

What, what sorts of magazines are we talking?

Real estate advertising.

SHAAN

Real estate advertising. Okay, give us an example.

All right.

SHAAN

So you got to carry one. You don't have one on you at all times? That's insane.

BRIAN

Yeah.

Real estate agents basically pay us to promote their listings. So magazine is like a lookbook of all the listings that are on the market at that time in their neighborhood.

SAM

And it goes to a lot of different, like, locations. Like, do you have different— 40 meaning—

Yeah, 40, 40 meaning basically we've divided the country into 40 locations. Yeah, zones. So we're covering all of the US and Canada.

SAM

How big is the magazine? Like, how many pages?

Anywhere from like 100 to 200.

SHAAN

Well, who's the reader? Because realtors are the ones advertising or want—

Realtors are advertising.

SHAAN

Who's the reader?

We, we have a mixture, but basically we mail the magazine out and we'll mail it out based on property value, income, things like that.

SAM

With the goal of being a real estate agent is— has a bunch of listings in New York City or something, I don't know, Dayton, Ohio.

BRIAN

Yeah.

SAM

And you want to show the resident of the homes on this block that they should either use this real estate agent or buy some of the nearby homes.

Yeah, either or.

SAM

Okay.

Yeah. Agents definitely are using it to pick up listings. Like they want to be able to say, look, I'm going to advertise your home, things like that. But they also want to sell the listing they have.

SHAAN

And what's it called?

SHAAN

Haven Lifestyle. Okay. How did you come up with this idea?

All right. So I started it with my business partner, Ryan. We were college roommates. I was a couple of years out of college. I was actually a bill collector for like 5 years through college and after.

SHAAN

A bill collector?

I was a bill collector, which I actually, I think really helped with sales. Like just having to call people all day for money, being rejected.

SHAAN

Are you like the muscle? Like what is a bill collector actually doing here?

Dialing them up. It was, it was credit card. So it's like Victoria's Secret. It's literally Victoria's Secret credit cards. But yeah, anyhow, I did that. I actually, I was a supervisor. I got drug into some HR nonsense that I couldn't believe and like having to basically defend myself. And I texted my college buddy. I'm like, dude, you want to do something? And he was like, yeah, let's, let's start the magazine. So that's where we started.

SHAAN

But why the idea of the magazine? He was already doing it?

He had a small publication in Annapolis, Maryland, and he said that basically agents had reached out to him and like, why don't you do something in D.C.? We want advertise in D.C., so we just launched one.

SAM

Who's the biggest? How many companies do what you do?

Most— there's a lot of small publications. So like each city you go into will have like a publication, but we have them across the whole country.

SAM

And you do $10 million in revenue. Can you say how much profit?

Yeah, like $2.5 million.

SAM

Okay. And the biggest one in the space is how big?

I don't know. It's not public. I don't— I mean, we could be one of the biggest in the space. Like there's not— most of them are franchised.

SHAAN

How many years you've been doing this?

SHAAN

10. Okay, so it's been a slow build. You've been steady at this revenue for a while.

It's been a slow build that, that has jumps.

SHAAN

Give us year 1. What was year 1 like?

$300K. And that's just me going, meeting individually, like just grinding it out.

SHAAN

Okay.

And my business partner handling everything else.

SHAAN

And did you know right away, like, this is it, I'm going to do this for a while? Or were you even after year 1, were you still like, I don't know?

I never thought $10 million, but I thought enough to support myself. Yeah. We launched an initial public— like we just did a free version of the magazine, like just Let us put you in. I'm gonna show you what it's gonna look like. And then I went around and had meetings all week. I'm like, here it is. And I mean, literally the very first meeting, the guy's like, alright, I'll do it. I was like, okay, cool. Like, I'm like 25 years old. Alright. And just meeting after meeting was like that. Got to a meeting where a guy's like, uh, what can you do for $10,000? Which is way more than we were charging. Like, how many covers can I get? So just like all of a sudden, like, I'm calling back to my business partner every few minutes. Like, dude, there's another, another, another. Like, there's something here. But I kept my other job for like 8 months.

SAM

But so, so the, it's more like a brochure, but it's a magazine because it's got a lot of pages, but it's a brochure. I mean, you're just showing off other, other people's stuff.

SHAAN

You're just sending a magazine unsolicited, correct?

There's not like a subscriber. It's true. It's no subscribers.

SHAAN

You're junk mail.

SAM

Sure.

SHAAN

Junk.

JOSH

Yeah.

It's not, it's, it's not a subscriber magazine. Also, I should say, I mean, that's like calling Victoria's Secret just underwear.

SHAAN

Yeah, exactly.

A huge portion is online at this point. Like, we do drive most of our traffic online, but everyone is paying to be in the magazine.

SAM

And who is doing— so let's say I want to be in the magazine and I like say like, yeah, I'm in. Who does the artwork? Who actually makes like the pages?

We handle it. Most of our designers are—

SHAAN

Philippines.

What's that? Philippines? Yeah, basically.

SAM

And how many of them are there? Because to have 40 magazines and how often, quarterly or monthly?

They're all every once every 6 weeks. We print 30 different magazines a month. Why did you just say— So every week we've got 7 going to prison.

SHAAN

Most of it's online.

Most of the exposure. So when you're talking about subscribers, junk mail, whatever. So like we mail copies out, we do that based on, like I said, net worth, things like that. And then we're also driving another, you know, 90% of our readers online, which are then looking for people that have like recently been looking for homes, things like that.

SAM

How many people work there?

SHAAN

So I'm confused. This is a dumb question. I don't really understand how junk mail works. So I can just mail anything to anybody?

You can mail anything to anyone.

SHAAN

So you just look up like, hey, addresses, like which zip codes or neighborhoods have a certain profile.

Yeah.

SHAAN

And then you download from some site all the addresses.

Yeah, it's all through the post office. Like you, you basically can pick postal routes and they'll deliver. It's actually cheaper when you do that.

SAM

How many magazines do you send a year?

Uh, like half a million. Yeah.

SHAAN

So this is the post office's business model, right? Like, yeah, basically the post office is pretty much funded by guys like you who are using it.

Like we have to make sure it stays within certain dimensions. It can't go over a certain amount of weight or it's a problem. The post office is Basically Facebook ads.

SHAAN

Yeah, exactly. It's Facebook. It's selling—

SAM

you are the product.

SHAAN

It's selling your address and your mailbox without you benefiting or agreeing to it to others.

SAM

What would it take to get you to $100 million in revenue? It's definitely possible.

SHAAN

No, no. Ask in the, like, Asian mom way. Why aren't you at $100 million yet?

Um, yeah, I mean, it's a good question.

SHAAN

Hey, I want to tell you about something pretty cool. We have a database of all of the unsexy business ideas that have been discussed on this podcast.

SAM

So hundreds of episodes.

SHAAN

The team at HubSpot went through, they pulled out all the unsexy ideas. So not the super high-tech ones, but the simple, relatable, interesting, profitable, uh, ideas that we have brainstormed. And they're all available for download for free. Just click the link in the description below. Thank you to our friends at HubSpot for sponsoring this podcast and putting together this free resource for you guys. Back to the show.

It's kind of a question I would have for you too, because I know you always say you get to $10 million. I know you can get to $100 million. So like, how? I think there's a few different ways. I don't think there's like one, like, switch, a flip of a switch. I think there's a lot of other verticals we could be hitting other than real estate agents, like home services, that sort of thing you're talking about.

SAM

Yeah, yeah.

Which we do within our publication. But I think if it was specific to their market—

SHAAN

You've told us about the business, magazine company, a.k.a. junk mail. You send it to people. What's the burning question? Like, where could Smart friends help you. Yeah.

I mean, honestly, I do think that question of how do you take this from 10 to 100?

SHAAN

Can I take a stab at helping you? So, uh, first I always want to know what's the default growth rate? Meaning how much did you grow last year to this year? What do we— what do I expect if nothing changes?

Probably like 10%.

SHAAN

10%. Okay. So to get to 100, or is your real goal 100? What's your real goal?

My real goal is to double profit.

SHAAN

Double profit. Okay. So you might not even need to grow top line.

We grow profit faster than we grow. Revenue.

SHAAN

Yeah. It seemed like when Sam was asking you, like, who's the biggest at doing this? And you're kind of like, ah, we might be the biggest. One thing that I can immediately tell that's very different about you than the way both— both me and Sam are reverse engineer type guys. We like to understand what's working for others, how big other people are, to give ourselves— like, we create this almost like box. And I feel like you don't do that as much. Is that fair?

Definitely. Yeah.

SHAAN

Yeah.

SAM

But you're happy.

Yeah, super epic.

SHAAN

What I mean is like, to be clear, we have a sickness and you seem fine, but we'd like to infect you with our sickness.

SAM

He doesn't need to change.

SHAAN

Yeah, yeah, yeah. But if you did want to change, here's what I might do. I think what I would do is maybe it's not like direct, like, oh, who also sends home listings, sells to realtors, but just the general model of mailing out magazines or informational stuff. To homes and generating a big business off the back of that. Who else does that? That's not exactly your space. Like, yeah, are there like wealth management companies that grow this way or is there some other category that grows this way?

I think the most— I mean, it's a little different, but I think the most intriguing are like neighborhood publications. So I don't know if you've heard of Stroll, but they do like—

BRIAN

Revolution?

SAM

Is that one?

I don't think it's Revolution. There's Stroll. There are others.

SHAAN

Is this kind of like what's going on in your area?

Exactly.

SAM

Years ago I talked about this. I think it was called Revolution. It was a neighborhood publication that's a franchise model. Model that, back then, we, I think we were in real life when we did this, actually, it was like north of $100 million.

Yeah, they're, they're definitely over $100 million.

SAM

My gut tells me that if you did have dedicated home services, that would be much.

SHAAN

And maybe there's a way to do it more informationally. So instead of the one you do right now, you're just like, here's the homes for sale. It's kind of like utilitarian. If you just said like, hey, here's all the home service providers, that wouldn't be that great. But if it was like, let's say it's winter and it's like Here's the 5 tips every homeowner should do for, like, listicle type of content.

Right.

SHAAN

And then on the inside there's providers, but like, you just do something that's actually like the ad. The front cover is basically like free, a give. It's, it's useful information, entertaining, useful information about, about home service or home care.

Yeah.

SHAAN

And then inside you obviously have home care providers where if people don't want to do it themselves, they could hire pros to come do this stuff for them. I wonder if you could get good at that. But I would just kind of— if I was you, I would start with a— not an answer, but a study. I would go get real familiar with what are all the other players doing in the space? Who's big, who's not, who used to work there? Go talk to them, go learn from them. Like, I would kind of go on like a, like a 1-month expedition of that. And I think you'll know so much more by the end of that.

SAM

Him and I are buddies. We talk about hiring all the time. I'm like, just go recruit someone who's at the bigger company and just have them come and work for you. Yeah. Why? And is there a world where instead of 40, it could be 80 markets?

It would be dicing the— well, we could go international. We're already in Canada. So there are markets that make sense for us to go into. But as far as 40 to 80, you would then break down the 40 into 80. It's the same geographical area. It's just going to be more because, I mean, we're literally covering the whole U.S. Got it. But I do think if you break it down, it's going to resonate more like there are areas that we have full states combined together. Because it's just not like Ohio, Indiana. It's just not that sexy of a market.

SAM

Would you ever sell this?

I would. It's not necessarily my goal. I'm pretty happy doing it forever. Yeah.

SAM

God, it's crazy.

SHAAN

You might be too happy.

SAM

It's crazy talking to, like, an emotionally stable person.

SHAAN

Yeah. You, you wanted to double profits, and I wonder what would happen again. I think this is more psychological than strategic, and I think people underrate how much of entrepreneurship is psychological and not strategic. I wonder if you just decided that instead of 25% net margins, you're going to have 35% net margins in the next 6 months. What would happen differently? Because I think you— I think right now my read is that you would like for there to be more profits, but you don't really have like a, I have to have more profits by this date. And if you literally just change the way you talked about it and thought about it, I'm sure that the answers would become pretty obvious to you as you started. Is that true? Like, do you have a— A goal and a date where it's going to happen by?

Yes, but it is, it is more recent change in the mindset.

SHAAN

So what is the goal and the date we can hold you to?

It was 1 year from a month ago. So it's, we got 11 months to double. Yeah.

JOSH

Double profit.

To be at a double, double as in double the run rate at that point.

SAM

So get to $4 million in run rate profit.

$5 million. Yeah.

SAM

$5 million.

SHAAN

How's the first month been in terms of, uh, If we were saying like out of 12 months, you've already used whatever, 8% of your time. Are you like doing what you needed to do to create a bunch of momentum or not really?

It's like, yeah, I think so. The main thing, the easiest way to double profits right now, I think, is retention. We already work with 10,000+ agents every year, but we don't get them to advertise that many times. So, I mean, literally double retention and we're fine.

SHAAN

You have the inventory yourself.

Exactly. We have, we have the clients like we have people that are agreeing to advertise with us.

SAM

Do you ask them multiple times?

Yeah, we ask them every, every cycle.

SHAAN

Why don't they just do it again if they're, if it's a money breaker for them?

A lot of times they just want, it's like, you know, I've got a big listing, great, now's the time, and then they just drop off.

SAM

Do you ever pre-sell them on, like, instead of, um, this one time, you say, I'll give you a discount if you do it for 12 months?

Yeah, yeah, I, we have like 1,500 people that do it for the year. So they're just on auto debit. So there's a decent amount doing that, but I think there's a lot of things we can do to improve their experience where they're coming back every month or just, I just need them to advertise one more time basically.

SAM

I wish you would have brought us one.

SHAAN

In the last, in the last, okay, let's say this year, how many of those agents have you personally talked to on the phone?

SAM

Zero.

SHAAN

Should I?

BRIAN

Yeah. Yeah.

SHAAN

Okay. Not necessarily to sell them, but like even just take your 100 top spenders. You should call every single one of them and figure out what do they love? What do they hate? Why aren't they doing it more? How do you get them? Are they actually— it's just been out of sight, out of mind. Oh yeah, I will do it. And you will learn a lot just by taking a roster of your top 100. I also learned this in our recent business that, that, that's done pretty well. I asked the CEO, I was like, hey, like, this has gone pretty well. What did you do? And he goes, you know what I did? I came in and he goes, I tiered out our key clients as tier 1, tier 2, tier 3. And he created a, a definition for each. He goes, tier 1 is somebody who's— they would do me a favor. I have them on a texting relationship. They know me, I know them. They would do me a favor, you know, quickly. Tier 2 is I got their email. We've traded some emails. We like each other.

SAM

We're acquaintances.

JOSH

We're—

SHAAN

yeah, we're friendly acquaintances. Tier 3 is like, we're transactional. Like, when they need me, they call me. When I need them, I call them. We haven't really talked much because that transaction is infrequent.

Yeah.

SHAAN

And then there's Tier 4, which is like worse than that. And he's like, when you do that and you just score yourself like, oh, what would a, what would a really healthy relationship look like here? Or what would a really weak relationship look like here? And then you look at your top 100 and you realize, shit, we have no tier 1s, couple tier 2s, and everybody else is tier 3 or 4. Then it's like a wake-up call. Nothing bad's going to happen by talking to your top 100 customers, but a lot of good can happen from, from going and talking to them.

Yeah, I like that.

SHAAN

And you could do that in 30 days. You could talk to all 100 in 30 days.

SAM

What do you think? Are you impressed? Did you ever know that something like this could exist? No.

SHAAN

It's so simple of a business too, right?

Like, yeah, it's pretty simple.

SHAAN

I mean, it's just, they didn't even subscribe. I'm used to media businesses where it's like, first, I win their hearts and minds and I get them to listen to me regularly or read me every day. Then I get to make money. He's like, no, no, no.

BRIAN

Read this.

SHAAN

Yeah.

SAM

Read. Yeah.

SHAAN

Ah, he, uh, have you heard? That's incredible. Why are we doing junk mail?

SAM

You know Lindy?

SHAAN

The AI tool?

SAM

Yeah, yeah, yeah. The Flo, the guy who started Lindy's in Hampton, and he's like, Alex Daniels has the most impressive AI setup I've ever seen. Oh, and that's been like a little bit of a claim of fame that he's had.

SHAAN

What, what, give us a little sauce real quick. What are you doing?

Uh, we used Lindy to basic, to, to run the sales process.

SAM

So they don't have salespeople.

We do have salespeople, but they're on, they've shifted, but they've really shifted to a different focus basically, which is where I'd like them to be more of that customer experience and like getting people to come back. Uh, but Lindy is able to respond to the, every email that's coming in, follow up with it, upsell them, just go through the whole process. But yeah, it was, it was a big Lindy, which is what Flo was talking about. It's crazy.

SHAAN

That's awesome.

SAM

All right.

SHAAN

Appreciate you, dude. What you've done is awesome, dude.

All right.

BRIAN

Thanks, guys.

SHAAN

Hey, let's take a quick break. You know that feeling when strategy is done, the brief is written, everyone's aligned, and you realize someone still has to sit down and actually create all the content? That someone is usually you, and it's due tomorrow. Well, the Breeze Assistant from HubSpot can help. It works right inside HubSpot. You can draft campaign copy, blog posts, emails, all in your brand voice. All using your actual customer data. So you don't create just content, you create content that converts. Check out HubSpot.com, the agentic customer platform for growing businesses. We need like a name for this. Dragon's Den, the Shark Tank, the, the swimming pool, the denim dungeon.

Let's go.

SAM

The denim dungeon. What's up? What up, brother?

SHAAN

How's it going? How are you?

SAM

All right. Your name and the impressive number.

SHAAN

Hit us with the big number.

JOSH

Great. I'm Josh. I run Team Outsider. We acquire family-owned campgrounds, and this year we'll generate around $20 million of revenue.

SHAAN

$20 million in revenue. Okay, so explain like I'm an idiot because I kind of am. What do you do exactly?

JOSH

So, yeah, so we acquire campgrounds typically from families who are looking to retire. And campground, the majority of it is like a hotel, right? So we're renting different spaces. Some people come in their RVs, so they have effectively a traveling hotel room. We also have tent spaces and cabins that we rent to people who don't want to stay in a tent and don't have an RV.

SHAAN

Do you camp? When's the last time you went camping?

SAM

Like 10 years ago, but I appreciate it.

SHAAN

I haven't gone camping in like 20 years. So a campground is literally just a piece of dirt, right? It's the ground.

JOSH

We have amenities. So all of our campgrounds have stores. We typically have a cafe where we'll sell ice cream and sometimes burgers and pizza.

SHAAN

Like cabins, basically, or—

JOSH

We have cabins as well. Yeah, we have swimming pools, lakes. At one of our campgrounds, we have a go-kart track.

SHAAN

Okay, so it's a very outdoorsy hotel, essentially.

JOSH

Effectively, yeah.

SHAAN

Okay, we're looking at one here. What's like the most popular one you guys have?

JOSH

They're all really popular in their local communities. The first one we bought, which is right near Grand Teton in Yellowstone, is really popular because that's a major tourist destination. We have one right outside New York City called the Neversink River Resort, a couple of hours away. So that's really popular with folks who live around here.

SHAAN

So give us a, give us the story. What makes a guy want to buy a campground? How do you even realize that that's a good opportunity?

JOSH

Yeah. So I met my partner in college, Cody. We studied together and started a business together, which was tremendously unsuccessful, but showed us that it was really good relationship. And so we stayed friends post-college, got some working experience, and then realized we wanted to do something together again. We were looking for a business where two non-technical founders could hopefully have a winning situation, and we wanted a market that was large enough to participate in and interesting, one where there was an immense amount of fragmentation with ownership, one that was operationally complex, and one that was meaningful where the team members would feel good working there and where the customers would feel good about being part of it as well.

SAM

So how many do you own?

JOSH

Currently we have 16 and there are about 4,000 sites amongst those in 10 states.

SAM

And did you raise money?

JOSH

Yeah. So the first one we did with our own cash and an SBA loan. So just kind of—

SHAAN

that was the Yellowstone one.

SAM

How much was that?

JOSH

About $3 million.

SAM

And so how much money of yours and loan did you put?

JOSH

The loan was 80-plus percent. Yeah, the rest was cash.

SAM

Sorry.

SHAAN

So that was an already operating site.

JOSH

Everything we buy is existing cash flow. It's been there generally for decades. Most of these are staples within their local communities.

SHAAN

So let's walk through that first one. So you find this property, it's doing what when you buy it?

JOSH

It was generating around half a million dollars of top line of total income.

SHAAN

Top line. And then the cash flow on that's what?

JOSH

About 35%.

SAM

Can you do that for me?

JOSH

Yeah, we call it $150K.

SHAAN

Okay. And you buy that for $3 million. Okay, so that's, that's the entry. And then you do that knowing, hey, we think we can turn that $150K into $250K. What was the, the insight at the time?

JOSH

Yeah, so that one didn't have a lot of digital marketing. It was—

SAM

was it like a mom-and-pop thing?

JOSH

All of them are.

SAM

And it's all— everything's on paper and they've been doing it forever and they're like, our kids don't want this shit. Do you want it?

SAM

And what are we going to do to make it better? And what is— what does better mean?

JOSH

Yeah, so there are a few things we can do. One of them is introduce just professionalized systems. So digital marketing, a better website, voice— VoIP systems for the phone to be able to make sure that the training is happening the right way.

SAM

Does marketing mean like Yelp and Google reviews?

JOSH

Google reviews, but also paid ads, a better website. Oftentimes there's no digital reservation systems. We'll introduce that.

Got it.

JOSH

So that's kind of on the technology side.

SHAAN

I think I missed it. So you're like, I wanted to do something with my friend and then you had the like business school explanation, like high fragmentation. But no, no, no. Like, where were you sitting when someone was like, should we buy campgrounds? Or like you met a guy who was rich that bought campgrounds. You're like, we should do that shit. Like, what actually happened?

JOSH

Great question. So our backgrounds were in hospitality and real estate.

SHAAN

Okay.

JOSH

So there's like obvious confluence there. And then Cody lives in Bozeman, Montana, and is an avid RVer. So he said, hey, like, the thesis sounds interesting. Why don't you fly out here and let's drive around the country, meet some owners, team members, guests, and see if this is something that actually has a little bit of a spark to it. So I flew out from New York, spent some time on the road meeting different campground owners and team members and guests, and just fell in love with the space.

SAM

And how much money have you raised in total now?

JOSH

We have raised Around $60 million.

SAM

You raised $60 million from our—

SHAAN

what'd you say, 15-ish properties?

JOSH

We've sold a couple, but we have 16 currently.

SAM

And what is it all worth?

JOSH

North of $100 million.

SAM

Does that mean that $40 million is you and your partner's equity?

JOSH

No, we've raised outside capital. So at this point we have family offices we work with, we have a select group of accredited investors we work with, and we have a few institutional partners that we've worked with as well.

SAM

I guess what I'm saying is of the $20 million in revenue, or if you value it— I'm not— I don't know anything about real estate. However you value it, how do you get personal personal cash flow or net worth from it?

JOSH

Like most real estate operators, it's promote-based, and different deals are different depending on the investment partner, right? So we are back-end incentivized largely for most of these, uh, typical private equity structure where there's a preferred return, there's a return of capital, and then there's a split depending on kind of who the investor profile is.

SHAAN

And so when you do that first one, you go buy it for $3 million, it's doing half a million in revenue, $150K of cash flow, What happened? What was the like success story of that one? Obviously it was a success.

SAM

Yeah.

SHAAN

You wouldn't have 16 more.

JOSH

Well, we were able to refi a couple of years later, so took all of our cash out.

SHAAN

You brought the income, the NOI up to what?

JOSH

The NOI in that one went from closer to, closer to $300,000 at that point.

SHAAN

Okay. So you doubled the profit on the, on the thing, recap, refinance it out, use that capital to go buy the next one.

JOSH

Exactly. Exactly.

SAM

That's pretty awesome.

SHAAN

Why are campgrounds— if I wanted to go do real estate, why would I choose campgrounds instead of whatever, retail shopping, multifamily, office, whatever. What would, what would be my advantages if I was going into this?

SAM

Will you do this for forever?

JOSH

I hope so. Like, yeah, you just— I love it.

SAM

Like, like looking down 10 years or 20 years down the line, where do you hope to be business-wise?

JOSH

Yes. Look, I think the, the larger opportunity as more of life moves online, I believe businesses that get people together in the real world are going to be more valuable. And there are different types of experience-oriented real estate that can speak to that thesis. But campgrounds still have a lot of runway. We still have a big pipeline of properties we'd like to be a part of. And so hopefully we're doing this for forever.

SHAAN

Who are the big dogs in this space?

JOSH

Yeah, so there are two very large REITs in this space that initially were into the manufactured housing side of the business, but recognized both from a depreciation perspective and also the infrastructure is very similar, right? You're renting—

SAM

there's a campground REIT.

JOSH

There are manufactured housing REITs that have a large portion of campground exposure.

SAM

Oh, that's interesting.

JOSH

Yeah. So that was one of the ways we were researching this that we got a little more comfortable with the idea.

SHAAN

When you're buying, you're buying out the operator and then you put a property manager, property management companies, or the manager. You are the manager.

JOSH

Yeah. So initially we didn't think we were going to go that route initially. So Cody, my partner, went and managed our first location for the first year, scrubbed toilets, did the whole thing, and we thought, you know, learn how to hold a shovel and dig a hole and then you can hire a third party to manage it like most real estate sponsors do. And what we realized is A, you can't outsource culture. So that was going to be really important for our success. And B, if we wanted to scale, there weren't really, at least at that time, competent third parties that could scale with us. So we made the decision to build an opco in-house and have been managing our properties ever since.

SAM

Your branding is cool. It's awesome.

JOSH

I appreciate that.

SAM

And when I was looking, I was like, oh, I would like to go see this. Is there a world where you would buy, buy many of them in a similar region and create a membership? You know, like KOA? Is it KOA?

JOSH

Yeah, we're actually a KOA franchisee in certain markets.

SAM

So how do I explain KOA to someone? I mean, I don't know.

JOSH

McDonald's of campgrounds.

BRIAN

Okay.

JOSH

They've got 550 flags across the country. They own about 50 of them themselves, but they are a franchise.

SAM

No, no, they're—

SHAAN

but is it like he's saying where it's a membership or it's just a brand? It's not a membership. You know what you're going to get.

JOSH

It's a brand you can trust and you know what you can get.

SAM

Yeah. It's like when I, when I do road trips and I want to camp, it's like something might be a lot nicer. Something could be a lot worse. But KOA, I just, I know what I'm rolling up on.

SHAAN

Like I was talking to a kind of like a famous guy and he was like, oh, out an hour outside of cities, there's something called, was it What is it, Postcard Cabins or something like that? He's like, oh, I love going to those with my kids. It's like, what's the, what's the story there? Then I looked it up. It's like owned by Marriott or something.

JOSH

They sold to Marriott last year. It's a little bit of a different model. They were focused on very remote single units in destinations where you didn't have to see your neighbors. We are more community focused. So a lot of our campgrounds have seasonal guests, which basically means these are people who reserve the right to a specific space for the duration of the season, pay before the season starts and come every year. Grandma's there, aunts and uncles are there, kids are there, everyone's been raised there, all the friends are around. So it's very sticky and communal.

SAM

But is there a world where you do brand it? So it's similar to each, each property has maybe a different shtick, but it's all under one brand potentially down the road.

JOSH

I think real estate brands are inherently tough to scale. Yeah. And until we have meaningfully more scale, that's probably not the right focus for us. But as regional concentration starts to happen, which is already naturally happening, Perhaps that's something to explore.

SAM

So when I hear you, I know nothing about real estate. When I hear you describe this, I think that sounds awesome. You're outdoors all the time. You're doing all this stuff. Obviously, that's not the case. What's the day-to-day work? Are you just like cold calling these places, trying to make a deal?

JOSH

Writing a lot of handwritten letters, a lot of cold calling, a lot of checking up on—

SHAAN

Have you found like a letter with a cookie converts better than like, you know, a call?

JOSH

A lot of it is luck. The challenge in this space is effectively our sellers are behind the front desk most of the time, which means in season they're exhausted and they don't want to take a call.

SAM

So the bottleneck of the business is just getting in touch and wooing—

JOSH

finding people who want to sell, building relationships and being the trusted succession plan because they care.

SAM

They don't care. It's not just a money thing for them.

JOSH

Exactly. These are their friends that they have been personally servicing for oftentimes decades. And so whoever's taking over that relationship is a really important—

SAM

is there like a— like a campground owners summit publication or summit or podcast. Yeah, there are Facebook groups and conventions and you're just like posting them all the time with like the same thumbnail image of across all of them. So everyone like starts saying like, oh, this is the guy. He seems like a good guy.

JOSH

A bit of that. We're trying to figure out how to do it in an authentic way. And that's a tough balance because there's a level of mistrust around being over-marketed to in this space. So a lot of it is catching them on the right day when the campground's a little bit less busy and they answer the phone and we can start a relationship and then, you know, years later when they're ready to sell, we got the call.

SAM

That sounds pretty awesome. Is this— how many hours a week do you work?

SHAAN

A lot.

JOSH

Yeah.

SAM

You grind?

JOSH

Oh, yeah.

SAM

You're in grind mode?

JOSH

Yeah, absolutely. But I love it.

SHAAN

There's a lot of real estate people, they choose real estate because while real estate is work, there's a way to do it or a state you can reach that is not about grinding. And it's about like you have a lot of flexibility and you got cash flow coming in or you're— you flip a property and you can take time off, you know, you could do all kinds of things. Sounds like you're approaching it more like company building than it is—

JOSH

Company building. And it's a hospitality business, right? We've got tens of thousands of guests every year, 350 people on the team. So there's no, no easy break period.

SAM

Is there— are the people you employ to run a campsite, are they pains in the asses? Like, are they hippies or are they meth addicts?

JOSH

No, we have some amazing people that work with us. We are—

SHAAN

We'll clip this and send it to them after you answer this question.

JOSH

Like, the majority of our team is incredible. They're aligned with our mission, which is to be the most hospitable team in the world, which when you're trying to replace a mom-and-pop operator is really important because the hospitality that a family provides is awesome, really tough to beat. But we do have some fun stories of team members that haven't been the right fit. We had a situation where we found out we had employed a convicted bank robber who had robbed 9 banks. I had to go personally fire him in person.

SAM

And what was that like?

JOSH

Terrifying. Yeah, he actually was incredibly nice and reasonable, but the drive in, I was very scared. Had another situation where we found out through a guest that some people on the team had been cutting down our trees and selling the wood for cash on a Facebook page. So it wasn't a great situation. And again, these are total outlier situations. They're just fun for conversation.

SAM

Hey, why do you live in New York? Why do you do this in New York?

JOSH

My family's here. My wife's here. My son's here. My parents are here. My in-laws are here. So, you know, when you have kids and the grandparents around— but my partner's in Bozeman and Look, let's hit it real quick.

SHAAN

What's the burning question? If you had a burning question, something that we can give you kind of a quick, maybe different insight on than as an outsider, what would be helpful?

JOSH

Sure. As you think about what we do in trying to scale culture to a team of hourly employees across 10 states with this workforce, what is something that we could do differently to keep people incentivized to deliver the level of service that we're trying to deliver? If you can solve this in 10 minutes, I will love you forever.

SHAAN

Well, actually, I'll give you a quick story. So my first business was a restaurant business, which has the same problem— frontline workers in hundreds of locations if you do it right. And we met with the founder of Chipotle, and he said, um, if you can get a frontline worker to care about the customer, like treat this the way you're treating this first location, you'll make billions of dollars. The problem is that's the hardest thing in the world to do. And Chipotle actually did some pretty interesting things where like both in the naming of it. Like, they have general managers. The general managers get comp. If any employee you ever have becomes a general manager, even if you don't longer work at Chipotle, you get $10,000 in the mail. Like, they do lots of things to, like, build a culture where they get people to stay longer than they normally would, to work their way up the ranks, to actually think like an owner of that place. And so I would just study. I'd make a list of the 15 companies that have already solved this problem. I would study what works. I'd look for common patterns, and I would try to hire people who were there in the early days, either as consultants or as a full-time person. Often you can find retired people who you're not going to hire them, but they kind of want something to do and they're sitting on this wealth of knowledge because they helped scale, you know, whatever, some cruise line. Sure. And, you know, and now they're just retired. And I think that's what I would do if I was going to solve this problem. My real-life answer is I run away from businesses that have that problem because I just, I'd rather pick a different hard. But you've picked this hard.

SAM

Yeah.

SHAAN

Good luck.

SAM

Have you read— obviously you've read Will Godero's Unreasonable Hospitality. We had him on the podcast and he told two stories that was interesting because I was like, okay, this works good in a fancy restaurant. Where else does this work? And he told two stories. The first one was he was like, I worked with a dealer, a Ford dealer, like a car dealer. And I worked with them. I go, look, let's just find like a forgotten moment where we could blow someone away. And I go, he will go, let's go sit in the car. Let's look around. He goes, what's in the glove box?. And the dealer was like, nothing. We don't keep anything there. He goes, I got it. Let's put a $15 Starbucks gift card in the glove box of every car. And we're going to put a note that says, we wanted to— whenever you go to open this glove box, we wanted to surprise you with something special. And that's all it said. The second example where he got his team to do it, he told the story of a UPS store owner. Not exactly a high margin or wonderful business necessarily, but he was like, every week the owner had a competition to whatever person did that was considered the most hospitable thing, they just got a $20 bill. That was it. And he was like, just doing that one contest, it changed the whole culture because now everyone was competing on who can be the most hospitable. And just like one little trick and like grown-ups are just like kids. We just like stickers. Totally. So and he told these two stories and I was like, oh, that's— those are so small. And he was like, they tracked like referral business and it, and it definitely worked. So he gave— you should listen to that podcast. It's My First Million, Will Godera. It was really cool.

JOSH

Amazing.

SAM

Look forward to it. But yeah, that guy's awesome. And he gave you like some actionable tips. Yeah.

JOSH

Fantastic.

SHAAN

Thank you. Right on.

SAM

Well, thanks for—

SHAAN

congrats on everything, man. Thanks for coming on.

JOSH

Appreciate it, guys.

SAM

God bless, dude. All right.

BRIAN

See you.

SHAAN

Should go camping.

SAM

Yeah, it's pretty awesome. A billionaire venture capitalist who's one of the greatest investors of all time. His name is Bill Gurley. He recently wrote about the single most important principle when it comes to building a company. It wasn't fundraising, it wasn't product-market fit, it wasn't even hiring. Bill said that an engaged peer network might be the most powerful growth tool available, but it's also one of the most underdiscussed is often underutilized. Now, keep in mind, Bill is a seed investor to Uber, Zillow, OpenTable. And so he's had a front row seat into how some of the best companies actually operate. And after decades of watching what separates the winners from the rest, he lands on this: who you're in the room with is the most important thing to whether you're going to be successful and build a great company or not. Now, most of you founders who are listening to this, you treat a peer network as something that's a nice to have, something that you're going to eventually get to do. But you actually never get around to making it happen. My company, Hampton, we have changed that. We build curated groups of highly vetted founders in cities across the United States, Canada, and England. This isn't a surface-level networking event. It's not a mastermind full of strangers. It's a peer group of 8 other entrepreneurs who will challenge you, hold you accountable, push you to grow, and you'll meet with every single month in your city. Apply at joinhampton.com/mfm and I will reply in the next 24 hours to help figure out if there's a good group in your city that's the right fit.

All right.

SAM

All right. The last one is going to be funny. All right.

BRIAN

How's it going?

SAM

What's up?

SHAAN

All right. Welcome to the hot seat. The denim den.

BRIAN

The denim den.

SAM

Let's go.

BRIAN

Is it live right now?

SHAAN

The dudes in denim, we're live. Let's go.

SAM

All right. You want to give us the big—

BRIAN

All right. The big number. I'm Brian. I run a company called Autopilot. We manage $1.8 billion and that makes $30 million per year of revenue for the company. We started about 3 years ago for the company Autopilot. And one number that kind of blows my mind, I think it's a testament to how much people want to invest in retail traders. It took Bill Ackman and Ray Dalio about 10 to 15 years to start managing $1 billion. And the fact that like Autopilot, this tech company that plugs into your Robinhood account, your Schwab account, could manage $1.8 billion to me just blows my mind.

SAM

I'm shocked. That's crazy. I didn't realize how big you guys were. So what's the business do?

BRIAN

Yeah, so the business we're most popular for launching the Nancy Pelosi stock tracker on Twitter.

SHAAN

I thought your big number was going to be Like 44%, that's Nancy Pelosi's annual returns, or, you know, what are her annual returns? What does Nancy Pelosi do?

SAM

In your app, I can invest alongside her picks because she's a politician.

BRIAN

So exactly.

SAM

So there is she. She's not a politician anymore.

BRIAN

So her— well, she retires in January of 2027. So we have that much time to copy her trades and follow her trades.

SAM

But basically I can follow anyone.

BRIAN

You could follow anyone. So you could follow her, you could follow different politicians. We also take 13 apps from different hedge funds. And that was the way that we kickstarted the marketplace. I think every startup has like that chicken and egg problem they have to solve. For a marketplace, you have the supply side and the demand side.. And if you don't have anyone to follow, that's good. You're not going to get people to come follow that person. But if you don't have anyone to follow, no one's going to want to launch on your platform. They're like, why am I doing this? So we were like, Chris and I, we got together and we're like, let's just manufacture the supply side. Let's take publicly available information.

SAM

Because the whole premise of Autopilot was anyone can become a— is that anyone can become a hedge fund?

BRIAN

Exactly.

SAM

And so instead of like having a Substack newsletter where you could follow my content, I can charge a certain amount and you could follow my trades or my portfolio that I think is good.

BRIAN

Exactly.

SAM

Got it.

BRIAN

And I think there's a lot of Substacks. I'm sure we've all like read some of them, but you don't know like the performance of this person. Maybe they're right and they'll always— they might be the winners.

SHAAN

They write a very convincing case and then they talk about how last time they were right, but you only know their cherry-picking winners.

BRIAN

They might have been wrong like 3 or 4 other times for that one. And so with Autopilot, you have a track record of success. You can see people's winners or losers, their performance, their entire performance, and then you can see how many dollars are following them, their content, etc.

SAM

How much money have you raised?

BRIAN

We've raised about $16 million.

SAM

One six.

BRIAN

Yeah, one six, $16 million.

SAM

And $30 million in revenue seems like a good company.

BRIAN

Yeah.

SAM

What's that worth?

BRIAN

I don't know. We're going out to raise a Series B. The valuations at different venture firms have, you know, floated around between $300-400 million, which is crazy, but that is venture money. Not sure what it's actually worth.

SAM

How old are you?

31.

SHAAN

You start this business. What was the first idea you had here? First idea is what?

BRIAN

So the first idea we actually started 6 years ago was an idea. It was a company called Iris. Iris for the eyes. So you could see into other people's portfolios. I was trading on Robinhood.

SHAAN

You've been thinking about this idea for like 6+ years.

BRIAN

Yeah. Yeah. And I think like, like we all kind of any retail trader, I don't know if you guys invest in the stock market yourself on an app.

SHAAN

Yeah.

BRIAN

Anyone's like, there's stocks that just fly and it's kind of obvious. Like I remember buying Nvidia or buying Tesla and you're like, like some things are just obvious to younger people, but if you just like don't do the research, you're not going to get those asymmetric gains.

SAM

Yeah, but most people don't do the research.

BRIAN

Most— yeah, most people don't. And I think most things I think are obvious are wrong.

SHAAN

Most of the time when I invest, I lose money.

BRIAN

That is fair. And there's— do you have like the inverse Cramer effect?

SHAAN

No, no, no.

BRIAN

But I think, I think there are certain people who just have a knack for it. And I think we were talking earlier about like how most people people should just invest in index funds. I would say I think that's true for the most part because a lot of people want to do it themselves, especially I think there's this advent of DIY. But I think the goal is for autopilot, for you to find someone who you have confidence in and can see the track record of success. You put like 10 to 20% of your net worth, not all of it, but in about 10 to 20% in these high-risk, high-reward strategies.

SAM

You know what's fun? Wait, so we're doing this Ray Dalio thing tomorrow. We're interviewing him and he started as a newsletter. It was like a $1,500 a month newsletter that SmartPants— and then someone was like, hey, if you think you're the man, then why don't you have your own fund? And like, you know, and he's like, maybe I will.

SHAAN

And now he has the biggest one.

SAM

So my question is like, why doesn't— I think, you know, Motley Fool. So Motley Fool does 9 figures a year in subscription revenue. So for you don't know Motley Fool, you give them $100 or some amount of money and they give you stock picks. But they also have a fund where they invest in their own picks. And I think they have over $1 billion AUM. It's all public. You can like look it up. So will like every financial blogger who like is a stock picker like be an Autopilot person?

BRIAN

Yeah, I think that's going to happen. We have—

SAM

then there's going to be way less of them because everyone's going to be able to see who's legit and who's not.

BRIAN

See, exactly. And so we have a 6,000-person waitlist to like launch a portfolio on Autopilot. So we do a lot of due diligence. We look at the track record of success. We'll look at— we'll analyze their actual portfolio because, for example, if you run a newsletter but your actual portfolio is bad, we don't really want you on the platform.

SHAAN

Who's the most famous or successful person that launched their portfolio on here, not like you're tracking the politicians.

BRIAN

There's a guy named Peter Wolf. And so I checked out his personal Robinhood account and I was like, this guy's up 200%.

SAM

How do you check someone's personal Robinhood?

BRIAN

Just by like, I would go on a video call and I would look at it. But right now we have tech where he could actually connect his Robinhood account to our platform and we could analyze it.

SHAAN

And 200%?

BRIAN

Over, over, over 3 years. And I was like, all right, 200% over 3 years.

SHAAN

That's a pretty small amount of time, right?

BRIAN

3 years is like— Yeah. A lot of people, right? And it's like, what does it do in a downturn? But I liked the way he was thinking about what he does to hedge against risk. And I was like, you know what, like launch on the platform.

SHAAN

You guys are kind of like you're, you are like the editorial team. You're the American Idol. You're letting them sort of audition. You're picking, right?

BRIAN

Yeah.

SHAAN

So you're picking the pickers, then they launch their portfolio. People then pay upfront to do it, or people just copy the trade and you get it. That person gets a commission.

BRIAN

Yeah. There's like a subscription fee, very similar to Substack. How much? Um, the pilot could, we call them pilots, they could set it. It ranges from $100 a year to $500 a year.

SHAAN

And so they do that.

BRIAN

Uh, how much are the top people making as the top people are making around $1 to $2 million per year on Autopilot.

SAM

Whoa.

BRIAN

Which is insane.

SHAAN

That's outside of their stock. That's just their Autopilot revenue.

BRIAN

That's just their Autopilot.

SHAAN

And so they, and so that's like, that means they have how many subscribers? Like 10,000 subscribers?

BRIAN

100,000? It depends on how much they charge. But for example, Peter Wolf has around $220 million following him on Autopilot.

SHAAN

Oh, so you see like how many dollars are backing you?

BRIAN

Yeah. And so again, for example, this is a stat that we pull. Bill Ackman, who traditionally raised a lot of money really quickly when he graduated Harvard, it took him about 5 years to raise $60 million. This guy on Autopilot within 1 year raised $220 million.

SHAAN

So you're basically— it's kind of like Justin Bieber was YouTube native.

Yeah, right.

SHAAN

He was a YouTuber first, then became Justin Bieber. And you're basically saying like the next Bill Ackman, the next generation's Ray Dalio is going to come from— it's going to come like ours or from you guys.

SAM

Do I put my money into Peter's fund?

BRIAN

Yeah. So what would happen is you connect your Robinhood account or whatever brokerage you have and it, we, it automatically follows his fund. So when he makes a trade, we send a notification to your brokerage to automatically buy or sell that security.

SAM

Copy trade.

SHAAN

But it's not giving the money to the guy.

BRIAN

Yeah.

SHAAN

And that's actually your Robinhood. Yeah.

BRIAN

And that's how we are able to operate from a legal standpoint. Whenever you're giving custody of assets away to someone, the SEC gets really involved. Is that a brokerage? You have custody. That's when a lot of regulation pops up.

SAM

How old is the business?

BRIAN

Autopilot. We've been running Autopilot for 3 years, but the entire business, like, structure is 6 years.

SAM

So Autopilot has existed in 3 awesome years. Yeah. What's going to happen in 6 years when you have 3 shit years?

BRIAN

If we have 3 shitty years.

SHAAN

Like stock market shitty years is what he's saying.

BRIAN

I think what we see is the retail investor right now perseveres longer than they used to. 3 years is a long time. I would say if it was like 3 years downturn, like consistently, I feel like the whole world will— there'll be a lot of questions for the whole world.

SAM

But that happens.

SHAAN

It happens to like Robinhood and these other guys, right? Like, what do you mean?

BRIAN

I think 3 years straight, it hasn't really happened, but I think you'll see like 1.5 years happen.

SAM

So I think Robinhood almost died.

BRIAN

Yeah, I read that. Yeah.

SAM

But they, they didn't because they had raised billions of dollars.

BRIAN

Yeah. And they, they had an emergency funding round.

SAM

Yeah. So like it was a near-death moment.

SHAAN

When was that?

BRIAN

During the GameStop? Yeah, during GameStop. They were about to go under and I think they had raised $40 billion like immediately and— or not, sorry, $4 billion immediately.

SHAAN

Because they needed liquidity or what?

BRIAN

There's something with like being a brokerage and like the DTCC, not too familiar with it, but they're like, you need to post up this money. We don't have—

SAM

are people nervous to invest? Are venture guys nervous to invest?

BRIAN

I think what we've seen in venture is just the AI wave. And it's just not— fintech was sexy in 2020, 2021. Right now with our metrics, I would think it would be very exciting for venture.

SAM

Like we have some friends in fintech, like a lot of fintech companies make like no revenue. Like, you know, you could be like, what's the thing called? Wealthfront. And you could have billions of dollars in AUM and like your fees are so tiny that So you're making $30 actual million in revenue? Yeah. Or GMV, like, you still have to pay it up.

BRIAN

So right now, because we've launched our own portfolios where we take 100% of the revenue, like the Plosi portfolio is ours, so we get 100% of that revenue. Our GMV revenue is $30 million, but our Autopilot ARR is around $22 million.

SAM

Okay, so you have more real revenue than like, remember Ankur was doing Carry and like he had like a billion in AUM, but the revenue was like literally a million.

BRIAN

Yeah, I think, yeah, I know that's, that to me always blows my mind. I think the thing that's interesting about us is when you look at other traditional asset managers, they just put your money in like ETFs and like mutual funds and there's no real alpha they're trying to get you. So they can't really charge that much money because you're like, why would I go to them? Why don't I just go to Wealthfront that charge like 0.1%? And so with Autopilot, the reason you pay so much is because these people are there. The hope is that they outperform the market. And so I think the average AUM that people pay on Autopilot is around 3 to 4%.

SHAAN

Does Nancy Pelosi hate you?

BRIAN

Probably, I would say.

SHAAN

Did you guys interact?

BRIAN

Like, we've never—

SHAAN

no cease and desist even from her?

BRIAN

Like, no.

SHAAN

Wow. All right, perfect.

SAM

Oh, she's getting soft.

BRIAN

I mean, the goal is when she retires, we try to have her actually join the fight and have a commercial. That'd be incredible. We, we did sponsor the UFC and got a fake Nancy Pelosi.

JOSH

Did you see this?

SAM

This is—

BRIAN

no, um, and so the, the goal was, this was the UFC before the election, and Trump was supposed to sit row 1 at the UFC. And we were like, wouldn't it be funny if we sponsor the UFC and it shows Invest Like a Politician right in front of Donald Trump? And then we have a fake Nancy Pelosi right by him.

SAM

Like, you bought a ticket? Or—

BRIAN

Oh yeah.

SAM

Or as part of the sponsorship.

SHAAN

So we had the ring sponsor.

BRIAN

Yeah, we had the ring sponsor.

SAM

Yeah.

SHAAN

And then they hired a lookalike Nancy Pelosi and they had her walking in. They had like the— You had like kind of social content of her entering the arena.

SAM

Did you have to actually buy that ticket?

BRIAN

We had to buy that ticket. That ticket row 1 was $60,000.

SAM

$450,000. No way.

SHAAN

How much you spent on the whole marketing buy?

BRIAN

About $450,000.

SAM

Did it help?

SAM

So that makes sense.

BRIAN

There was. And I was like, dang, he's not here, but I'm glad he's safe. But I think if he did show up, I think the, the media that would have been picked up, the earned media would have been insane.

SHAAN

Hey, it was ballsy. And sometimes you got to do what you got to do. I think it's cool. We're still talking about it now, right?

BRIAN

Exactly.

SHAAN

That's attention. That's fair. That happens when you do unique, over-the-top things. So that's amazing.

BRIAN

We're trying to think of the next stunt, but most—

SAM

How many people work there?

BRIAN

Right now, 30, 35.

SAM

So you're doing $800,000 of revenue per—

BRIAN

It's about $1 million per employee.

SHAAN

Walk me through the like What does this look like if this is actually big? Because some of the weird ideas here— this is a weird idea. Yeah. And weird ideas have a lot of potential, even though on the surface it takes a little time to like understand.

BRIAN

I guess to me it was kind of like a common sense idea. Like, I don't know, growing up I was like, man, why can't my Robinhood account just like follow this other guy's Robinhood account automatically? Like, I don't want to just give my funds away to someone else. Like, I want to be able to do stuff myself, but I also want to like go on vacation without worrying about like when to sell or when to buy. I think the solution to me was just the most obvious. But I think the ultimate goal of Autopilot is to become the world's largest asset manager. When you look at BlackRock, they actually do this for institutions. BlackRock connects all these financial institutions. Companies will go on a tool called BlackRock Aladdin and buy different portfolios. So it already exists at the institution level.

SHAAN

They buy different portfolios.

BRIAN

BlackRock will create their own portfolios based on different risk. And so like if you're Walmart and you're, you know, heavily invested in you know, groceries for this quarter, you could actually like hedge your bet on BlackRock Aladdin. If you're a Facebook employee, you could actually find a portfolio on Autopilot that hedges like tech. And that tool that BlackRock created makes around $6 billion per year. And BlackRock's one of the largest asset managers. And so I think with Autopilot, one of our goals is to get that same tech and like build it for retail investors.

SAM

How do you get those? How do you— how are you going to hire those people?

SHAAN

Well, he's saying people come to the platform like two-sided marketplace.

SAM

Yeah.

BRIAN

And so then the pilots come and they're the ones with the ideas. You verify, you know, their employment, where they've worked. But really the goal is where anyone could just publish those portfolios and get paid. And then us as a marketplace, we take a cut of that revenue.

SHAAN

What would be the burning question?

BRIAN

I have a bunch of large macro questions on AI, but I also have questions because you guys have been running companies for 10+ years. One of the biggest things is hiring. How do you find people that are highly motivated? What questions do you ask? Because one thing that I've noticed is when you hire especially more senior level people, their ability to BS is greater than my ability to detect BS. And I think there are certain questions or certain things that you could look at that you guys probably have more experience that would actually really help Autopilot get to the next step.

SAM

Well, for one, having like a personal audience is like definitely that's probably one of the biggest perks is that you're able to like if you cold email someone, they're like, oh, I've heard of you or I know of you at the very least. At best, you have a lot of people who apply. But whenever I would hire for people who, uh, roles that I didn't know what the hell I was doing, I definitely would have like an outsider hiring committee. So I would have outsiders, uh, interview people all the time. And that helped me a lot.

SHAAN

Yeah, that was going to be one of my— I've probably 3 or 4 tips. They're not all related. The first is I find a lot of my hiring mistakes where I didn't actually even understand what I was hiring for. I wasn't clear enough. Sometimes that comes from I do the work for a little bit and I'm like, oh, okay, what the person's going to need to do is X, Y, Z. As you scale, that happens less. Uh, but still writing down, not like a generic, like I think a lot of people outsource the job spec to either ChatGPT, a recruiter. It's super generic. It's going to attract a generic candidate and it's not actually clear. What are you, what are you trying to get somebody to come change in your company? What do they need to be world-class at? What sort of problem are they going to have to solve? And be really, really clear. So that's the first thing. Second is kind of yours on outside, uh, help. So I have a buddy who, he's better at hiring than I am. And so what I would do for any executive hire is I would call the favor, be like, hey, like, once I've done the screening, will you talk to these— will you talk to my favorite kind of 3 or 4 candidates and give me your take? And it really wasn't about who he picked. It was me becoming a better hire and interviewer by understanding the delta of like, I thought this person was great. He sniffed out their bullshit really quick. Why did he do that? And I'm watching the call and I'm realizing like, oh, he dug in in a different way, asked a different style of question, didn't accept their first answer at face value. I got to start doing that. And so I got better by doing that, not just because they helped me pick this person, but because I realized where I was weak in the interviewing process. I also think there's two really good pools to hire from. One is you want people who've either done it before or never done anything but can do anything. So done it before is Who solved this problem before? I always start there because if I can find somebody who's already done this before, that's going to help me a lot. And I mean specifically. So it's not just like, oh, he worked at a successful company, but they do enterprise sales and we don't even do enterprise sales, right? It's like, no, they solved— they did this exact thing before this.

SAM

We've talked about this a lot in the pod where it's like, it's so fun to hire young people. They don't have any experience. It's so fun, right? Because that's what you were recently. But like 9 out of 10 times, if you're just like, like, hey, you did that there, do that same thing here.

BRIAN

Right.

SAM

And that tends to just be way better.

SHAAN

So we will map out which companies have solved this problem before. Who was the person that was there at the year when they had this problem where we are? Who was that person? And then were they the real shot caller on the team or were they just doing something? But there's somebody else who was amazing. I like go to that level of detail there. So that's one pool you got to get good at. And the other pool is like basically diamonds in the rough, like unproven talent that you can almost be a stock picker on and be like, okay, I think this person's like a 10xer and I build the company with those two pools of people. And you build systems so that you consistently are sourcing from both of those.

JOSH

Yeah.

SHAAN

Most of the— one thing most people— are you the CEO of the business? How much time per week do you spend recruiting right now?

BRIAN

Right now, about 20%.

SHAAN

That's pretty good. Most people— that means one full day a week, basically.

BRIAN

Yeah.

SHAAN

Most founders who have like hiring problems, if you ask them that question, they're like, hours.

BRIAN

I think it used to be that. And now I'm like seeing how important it is.

SHAAN

And if you listen to like a lot of the most successful founders that were in a scaling phase, they spend like 30+ percent of their time just on recruiting.

SAM

Are you guys profitable?

JOSH

Yeah.

SAM

Okay, so you're at $20 million in revenue or $30 million.

JOSH

$30 million.

SAM

$30 million in revenue.

BRIAN

Cash flow positive, not like GAAP profitable, but—

Sure.

SAM

So you're default alive. Yeah. What's the growth rate going to be this year over the next year?

BRIAN

About 250%.

SAM

I would think almost your entire job is collecting people.

SHAAN

What sorts of people do you need to be hiring right now?

BRIAN

A lot of software engineers, product people. Growth people, marketing people, really anyone. But I think people, people, just people. I think the thing is, is just maintaining that high bar. And we've just hired a lot of people and perhaps I'm actually very quick to get rid of people if they like come in and within like 2 to 3 weeks they haven't really done anything. I just immediately I'm like, all right, you're getting out of here.

SAM

Is that impact that impacts culture, which is why you got to get the hiring right?

BRIAN

It impacts culture. But I think everyone who's been here Anyone who we, we tell people, if you're here for longer than 3 months, you don't have to worry. So I think after the 3-month mark, people are like, okay, I'm chilling. But before that, everyone's like freaked out.

SAM

Are you going to only hire in New York?

BRIAN

Yeah, yeah, we, we, yeah, yeah, we've— I think especially with AI, the salaries that we're paying people, like we, we just, just offered a guy like a $350K salary and I'm like, this is crazy because I've never made that much money. I still don't. But yeah, I think the goal is with AI, each person is much, much more effective. So a good person with AI could be 10, 20 times more effective than an average person with AI. That's crazy.

SHAAN

Yeah. My CTO used to say it too. He's like, you're one person. No, you're 3 people. He says, you're 3 people. He used to say that all the time. And people like, it's funny.

BRIAN

I might start saying that.

SHAAN

It's real simple. It's just people just realizing what you mean. It's like, no, you need to be able to do the work of 3 people because you got to be smart about what you don't do, don't do the bullshit, automate stuff, you know, figure out like a faster path. You know, that's your job is to be 3 people. And when we used to do offsites, we would say every day is 2 days, like 2 days of stuff needs to happen every day. And so I think when you do that, you set up a set of different bar for your team on how they operate.

SAM

Yeah, dude, thanks for doing this.

BRIAN

This is awesome.

SAM

You're awesome. We, I messaged him roughly 2 hours ago and I was like, where are you?

BRIAN

Yeah, I saw the post. I'm like, yo, Sam, I got to get on my first board.

JOSH

Where are you?

BRIAN

This is a dream.

SAM

Can you be here?

SHAAN

Well, you guys have— are one of the great, like, growth hack stories. Like, this is what you guys did with the Pelosi tracker. You have another tracker. Do you have other trackers?

BRIAN

Yeah, we have, like, you know, the Leopold tracker. Who's the best right now? Leopold. He's up, you know, same amount.

SAM

Is he like a 25-year-old?

BRIAN

He was like a 22-year-old. He worked for OpenAI. Now he's like 25. He left OpenAI and then started a fund.

SHAAN

Isn't he up like $10 billion or something?

BRIAN

Around $5 billion.

SAM

So he's a billionaire now.

BRIAN

I think so.

SAM

I think he raised outside capital.

BRIAN

I think of a lot of, a lot of it was friends and family, but Daniel Gross and Nat Friedman and like smart money was immediately behind him.

SAM

How much did he raise?

BRIAN

I think originally $500 million, not that much. And I was at like upward of $5 billion. But what he did, which was super smart, 10x in 2 years. Yeah. He looked at what companies, what was the bottlenecks of OpenAI and he was like, okay, well SSDs, like a lot of people thinking GPUs, here's like SSDs, like Micron. And so he just started buying all of like the other bottlenecks that no one was focusing on. And now they're just like skyrocketing.

SHAAN

And isn't like his— somebody is like the chief of staff at Anthropic. He's got some, some information flow as well. That's pretty good.

BRIAN

Yeah.

SHAAN

I mean, he's brilliant. Have you read his like situational awareness paper?

JOSH

No.

SHAAN

Okay, so do this. Uh, I did this and it was very, very useful. Take the PDF for situational awareness. It was like on my list of like—

SAM

What is situational awareness?

BRIAN

Hedge fund name.

SHAAN

He published published a white paper or blog post, like a PDF before, like before he launched the hedge fund or right after. I think it was actually maybe before. And this is how he attracted the money. He launched this thing, which is basically he had a very strong point of view on like what the next 10 years of AI looks like. Very bold predictions. It was like, and then huge tension between China and America. And then because of that, this, it was like super specific predictions. Of how the puck, where the puck was going. So he published this thing and a lot of smart people were like, yo, this is like one of the smarter takes of what's going on. I think that attracted more capital, more awareness.

SAM

Situational Awareness was the name of his publication.

SHAAN

And I think it's the name of his, uh, his, his, whatever his company is. So take it, give it to, you have Victor in your Slack.

Yeah.

SHAAN

Just say, Victor, break this down into the 10 key ideas, like predictions and hypotheses that he has. Explain it and just explain it to me. Victor did a wonderful job. He like just chewed up this PDF for me. It explained it step by step. And then I asked follow-up questions and it was just great. And I was like, so did that play out? Was he right about this? Did he trade on that? And it just, it just answered every single question.

SAM

It was so good. Is a guy like him—

SHAAN

Victor, by the way, is like an AI thing that Sam put me onto that I am now hooked. I ended up investing in it.

SAM

Yeah, thanks for telling me. After I told you about it, you should have told me that.

SHAAN

Well, it was at an absurd valuation, but like, it's that good that I was like, yeah, for sure.

SAM

I told him about this tool. He's like, I don't know, I don't trust these tools. These are stupid. And then 2 days later he goes, these tools are awesome. Have you heard of this tool?

SHAAN

I made him feel dumb. I was like, why do you just trust a random startup with all your stuff? And then I heard about it a little more and I was like, let's try it out. And I tried it in one of my Slacks and I was like, this is amazing. Now it's in every business I have.

SAM

Yeah, that's good. But the, um, I'm curious about the personal, personal side on this. Is he like low-key right now? Is he trying to hide out?

BRIAN

No, he posts on Twitter.

SHAAN

Really? He did. He's like, he's like very good friends with Dwarkesh. So he's done the Dwarkesh pod a couple of times where, I mean, is he cool?

BRIAN

Yeah.

SHAAN

Do you think like Peter Thiel's cool? Like, you know, like, do you think a lot of Asperger's genius?

SAM

Cool.

BRIAN

Yeah.

SAM

Like that energy.

SHAAN

Yeah. He has that.

BRIAN

It's great.

SAM

I love it.

SHAAN

I love it. Yeah.

SAM

You can follow him on autopilot.

SHAAN

I'm saying, yeah, that's not the word I would use. I love it.

Yes.

SHAAN

I think he's awesome.

BRIAN

And so you can replicate his, you could follow his top 15 picks on autopilot. And how do you know his picks? So he filed a 13F and so it is delayed.

SHAAN

There's a little lag.

BRIAN

There's about a 45-day lag, but even we only track with the lag.

SAM

And a 13F, how big does your fund need to be?

BRIAN

Oh, $100 million.

SAM

Oh, okay. Damn. So he's the guy right now.

BRIAN

He's the guy.

SHAAN

He's the guy.

SAM

Does he do podcasts?

BRIAN

You actually get them on?

SHAAN

There's a couple. We're trying. I think we were reaching out. Yeah.

BRIAN

And it's stuff like this that makes me like very adamant of like people should always invest in index funds, but there should always be like 10 to 15% of your like net worth on high-risk, high-reward stocks or portfolios. And so this is where Autopilot doesn't right now want to take 100% of what you have, but just like 10 to 15%.

SAM

Your liquid net worth, where is it allocated? Who are you following?

BRIAN

Right now I follow basically like 20 different pilots on Autopilot right now.

SAM

So right now of your, of your 100% net worth.

BRIAN

So my 100% net worth, it's like 90% on Autopilot. A lot of it is in Autopilot.

SHAAN

I want to know the truthiness. So you said you connect with their brokerage account.

JOSH

Yep.

SHAAN

But like people have many different accounts.

BRIAN

Yeah. So you can connect to all of them. You could.

SHAAN

But, but you don't know if, if this is tracking all of them or just tracking some, right? Me as the user, I don't know if you have everything that this person has done, right?

BRIAN

Yeah.

SHAAN

So winners and losers.

BRIAN

So what it is, is the people will go on our platform and create a model portfolio. And so you only see the history of the model portfolio from when the pilot joins to now. So it's not like actually following their brokerage account. Oh, okay. But what we do have is we have what's called skin in the game where the pilot will also put their money on Autopilot following their own portfolio. And so you could be like, wow, Peter Wolf has $500,000 following his own trades verified by Autopilot.

SHAAN

Gotcha, gotcha, gotcha.

SAM

Are you having fun?

BRIAN

I would say right now I'm having fun. I would say the last 3 years have been— it's, it's hard. I would say getting from 0 to 1 million in revenue was the hardest thing I've ever had to do. Getting from 1 to 30 was actually a piece of cake.

SAM

What do you think the next, the next threshold will be?

BRIAN

I think we're on track to hit $100 million in revenue by March next year. I think it's going to be difficult, but—

SAM

Run rate?

BRIAN

Recurring revenue, not run rate. Right now we're at like a $70 million run rate, but we want to get—

SHAAN

I passed on investing in this like twice already.

BRIAN

Yeah, why didn't you do it? I know.

SHAAN

It seemed like a really hard thing to get off the ground. It was very hard.

SAM

How did you get away with this?

SHAAN

Well, I'm a degenerate and they listen to MFM, I think. So like, they knew that I'm a bit of a—

BRIAN

And you've talked to Chris a couple of times.

JOSH

I talked to Chris.

SAM

I really admired the marketing.

SHAAN

So I think I just reached out giving respect. I was like, hey, I think it's brilliant what you guys are doing with the Plus Tracker on Twitter and the UFC. I just thought you guys were doing a really good job without the marketing.

BRIAN

We wouldn't be here just because of how hard this stuff is to do.

SAM

What's your— what was the first round's valuation?

BRIAN

The first round was, uh, $7 million.

SAM

Really?

BRIAN

Yeah, but that was 2021. Like, there's a lot of, uh—

SAM

yeah, man.

BRIAN

Yeah.

SHAAN

Well, either way, I'm a fan, and, uh, I think what you guys are doing is great, man. I appreciate you coming on.

SAM

This is awesome. Awesome.

SHAAN

All right.

BRIAN

We appreciate you. Thank you, guys.

SAM

We'll talk to you a little bit. That was awesome. Good picks.

SHAAN

Yeah, that was cool. That was fun.

SAM

I hope this is a— this is a Hampton plug, by the way. I definitely just went into the New York channel and I just said, yeah, who's interested? Because I didn't want to tweet it out because I wasn't sure what we're going to get.

SHAAN

I'll do the plug for you. If you're an interesting business owner and you want to be in a community of other interesting business owners, join Hampton and maybe you too can be on MFM someday too.

SAM

Hip that I didn't realize how big Autopilot was.

SHAAN

I thought it's been scaling a lot. Like it wasn't that big like 6 months ago, you know.

SAM

Well, he told— I knew it was $30 million in revenue. I thought that meant like GMV-ish type thing. Because those businesses, not his business, but that category of business is usually pretty shitty, right? Like numbers can be huge, but the actual business— but not his. That's insane.

SHAAN

Yeah, he's doing well.

SAM

That was cool, right?

SHAAN

You know, one of the things with probably the biggest thing for me since I started My First Million till today was is I remember pre my first million, kind of like 10 years before that, the full 10 years, I felt like opportunity, like success was this needle you had to do in the haystack, or it was this narrow thing, this thing I had to search for in this room. And it was so hard to find. And I needed this brilliant idea. And if I just— is this the brilliant idea? Where is the brilliant idea that I need? Perfect execution. I remember opportunity just felt so scarce. And then one of the things of you move to San Francisco, you meet a bunch of people, we start doing this podcast, it's like you just realize, oh dude, there's thousands of different, tens of thousands of different ways that I can win. Opportunity is everywhere. It's really about picking what's the right fit for me. It was a total, like, from lack to abundance mindset shift on success. Like, where does success live? And like, what I like about a thing like this that we did today is those are 3 ideas that didn't even exist in my, my cone of vision. You know, I couldn't even— I didn't even know that people do businesses like that.

SAM

And there's also parts of their business and their lifestyles and personality that I want to like, like I love and I want to steal, right? But I don't admire the whole thing. Like, for example, Alex, I'm like, oh man, he's so calm. Like, right? Like, oh, I need to learn from that. I don't necessarily want to trade what I have for what he has, but like, I want to steal this from him.

SHAAN

And he wasn't in a rush. Yeah. Better and for worse, but mostly for better.

SAM

And same with Brian. Huge business taking off. I don't want to do all those stunts. I don't want to raise VC, but that's pretty awesome.

SHAAN

But I admire the creativity.

JOSH

Yeah.

SAM

And then like Josh's outdoor business, I'm like, that's awesome. I don't want to raise money, but like, it would be maybe fun to own one. Like, you know, like there's really small—

SHAAN

but I should go camping.

SAM

Yeah. No, but there's like small things, right? Like, you know, I think people sometimes in the comments tease us about like having— I hate when people say you have these guests that are out of touch. Whenever I hear that, I'm like, No, you're out of touch with his life.

SHAAN

Yeah, that's about you.

SAM

You're out of touch. No, what I mean is I'm like, I am equally impressed by like a billion-dollar company versus a $5 million company. They're all— they're both equally awesome.

SHAAN

Somebody, Jesse Itzler, said this at one of our events. It was like an intro. I said, hey, what does somebody— what do people— what should people know about you? Like, hey, I'm Jesse Itzler, blah, blah, blah.

I did this.

SHAAN

He goes, my thing is is I root for everybody, because when you root for everybody, you can never lose. And then he sat down and I was like, yo, I kind of like that fortune cookie shit he just did.

SAM

Is Jesse Itzler really a cool Black man?

SHAAN

Yeah, yeah, no, he's the best. It's cool Black guys like him. Yeah, it's like, whoa, that's like the next level. So in the same way of like, you, when you root for everybody, you can never lose, or something like, if you think you can learn from everybody, you can never lose, right? So it's I'm like, great, tomorrow we're talking to Ray Dalio. There's going to be some awesome things to learn from him. Again, parts, not the whole. We're not trying to do what he's doing, but I'm still going to pull something away. I'm going to get a win and I'm going to have some fun in that hour. Just in the same way I got wins and learnings and fun in this hour.

SAM

I think the new slogan should be we get, you know, high high and low low because I get like equal joy. Like we'll go to the, we'll like pop into a bodega. I'll love that shit. And now we're going to go hang out with like the AD of the richest person in the world. I'm going to love that equally.

JOSH

Right.

SAM

All right.

JOSH

That's it.

SHAAN

That's the All right, let's take a quick break to talk about a podcast. Because if you're listening to this, you like podcasts. And what's better than one podcast? Another podcast. And let me tell you, another podcast you should check out, it's called Success Story. If you like hearing about different success stories and hearing Q&A sessions with successful business leaders, or hearing keynote presentations, or just checking out conversations about sales and business and marketing tactics, this is a great podcast for you. So check it out wherever you get your podcasts.